I’m a total fanboy when it comes to great, tough reporters. Some of it stems from harboring fantasies of journalism as my “path not taken” but I also got to see the difference in skill levels from all the media covering Google/YouTube. The good ones are really good. The average ones are frustrating. Outside of the professional respect I hold for the good ones, they also have compelling personalities and backgrounds beyond the byline. Jessi Hempel and I have shared meals, hikes, drinks and panels. Here we share Five Questions…

Hunter Walk: Were you born a writer or did you become a writer? Either way, do you recall a specific moment when you thought “I want to do this as a career?”

Jessi Hempel: I was born a storyteller, but until the third grade, I was fairly confident I would be an ice skater. That year, I won the school writing contest for my essay on what I wanted to be when I grew up: though I had only been on ice skates once, I did a pretty good job of describing why it was the career for me. The principal handed me a trophy and told me I’d be a writer when I grew up, and it stuck. I believed her.

I studied creative writing in college, and was dismayed to discover, upon graduating, that it didn’t offer me a surefire way to pay my rent. I tried a bunch of jobs: I taught fourth grade, worked at a nonprofit, and made an ungodly amount of money doing odd jobs at a dot-com because hey, it was 1999. But I only wanted to write—the habit filled up all of my spare time, and eventually I understood that it was more of a calling than a profession. I was going to have to figure out how to do it all day, every day. So, I enrolled in the journalism program at the University of California at Berkeley.

HW: Early in your career you were a freelancer, but the last 12 years you’ve been a leading journalist at some great institutions (currently Wired; formerly Fortune, Businessweek). Besides a steady paycheck, what’s the value in being attached to a specific brand versus, for example, running your own shop a la Daring Fireball or Ben Thompson’s Stratechery?

JH: Over the past decade, I’ve seen the power relationship shift individual writers and brands. Individual bylines are more important than they used to be while big media brands don’t always have the strength they once did. This is happening, of course, not just in media, but across every industry. That said, I think we journalists can sometimes underestimate the power of traditional brands to provide strong platforms that amplify our voices and make us better journalists.

Wired’s digital platform had more than a billion unique readers last year; it also has the resources to support everything from the immense travel that went into this deeply reported feature on Facebook’s plan to wire the world to a new podcast that my buddy Tim Moynihan and I are preparing to launch. And most important, Wired has a community of creative, skilled editors and writers who make me better at my craft on every platform—these people really up my game.

HW: On some of the hot issues in tech – startup valuations for example – I’m sometimes surprised to see “techies” and “tech press” each assume a default position of opposing viewpoints. Is that a fair characterization in your mind? What’s changed over the last decade in terms of the role of the technology press? And why do tech workers seem thin-skinned (you can’t say “millennials”)?

JH: I think this varies widely from publication to publication, but that I have seen this gap widen as tech moves from its disruptor status in the economy to a more significant role as a primary engine of economic growth. The press has an important role to play in helping to hold technology companies accountable for the commitments they make to their shareholders, both public and private, and to their customers. That can create a productive tension that benefits the larger public.

And techies are thin-skinned, I won’t argue that. But I don’t know as they’re more thin-skinned than other business people who’ve been covered by the press over the past century. People react badly when you write things that depict them in a bad light, but if you say things are true, they almost always come around over time, and respect you more for it.

HW: You wrote “What We Need to Stop Talking About in 2016” — are there things you wished we talked MORE about in 2016?

JH: Yes! Yes, there are many things that I hope we talk more about. We need to help readers better understand the myriad ways in which companies are using their data—for the good, and for the bad. We need to do a better job of writing about where lofty valuations come from, what they represent, and how they will impact the longterm prospects of these companies, and the employees that work for them.

HW: Any recent pieces where you remembering thinking “Damn, that reporter can write!”

JH: There is so much awesome and smart writing right now! Like Fortune writer Erin Griffith’s profile of Nikesh Arora in which she opens with a description of a selfie swarm. Or my colleague Jason Tanz’ moving story about a man who built a video game about his son dying of cancer. And WIRED has an editor named Emily Dreyfuss who can clean up tough stories on security or business issues, and is also one of the funniest, smartest writers you’ll read. Check out her ode to Skymall, written as it filed for bankruptcy last year.